List of esters

Summary

In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (−R). Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well (i.e. esters of acidic SH, SeH, TeH, PoH and LvH groups). According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC.[1]

An ester of carboxylic acid. R stands for any group (organic or inorganic) and R′ stands for organyl group.

An example of an ester formation is the substitution reaction between a carboxylic acid (R−C(=O)−OH) and an alcohol (R'OH), forming an ester (R−C(=O)−O−R'), where R and R′ are organyl groups, or H in the case of esters of formic acid. Glycerides, which are fatty acid esters of glycerol, are important esters in biology, being one of the main classes of lipids, and making up the bulk of animal fats and vegetable oils. Esters of carboxylic acids with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties. Esters of carboxylic acids usually have a sweet smell and are considered high-quality solvents for a broad array of plastics, plasticizers, resins, and lacquers.[2] They are also one of the largest classes of synthetic lubricants on the commercial market.[3]

By number of R' group carbons (R−C(=O)−O−R') edit

1 carbon edit

Name Structure
Methyl nitrate[4]  
Methyl formate[5]  
Methyl acetate[6]  
Methyl acrylate  
Methyl propionate[7]  
Methyl butyrate[8]  
Methyl pentanoate[9]  
Methyl benzoate[10]  
Methyl anthranilate[11]  
Methyl salicylate[12]  
Methyl phenylacetate[13]  
Methyl cinnamate[14]  

2 carbons edit

Name Structure
Ethyl formate[15]  
Ethyl acetate[16]  
Ethyl propionate[17]  
Ethyl lactate[18]  
Ethyl butyrate[19]  
Ethyl pentanoate[20]  
Ethyl isovalerate[21]  
Ethyl hexanoate[22]  
Ethyl heptanoate[23]  
Ethyl benzoate[24]  
Ethyl salicylate[25]  
Ethyl octanoate[26]  
Ethyl cinnamate[27]  
Ethyl decanoate[28]  

3 carbons edit

Name Structure
Propyl acetate  
Propyl propanoate  
Propyl hexanoate  
Allyl hexanoate  
Isopropyl acetate  
Isopropyl salicylate  
Isopropyl palmitate  

4 carbons edit

Name Structure
Butyl formate  
Butyl acetate  
Isobutyl formate  
Isobutyl acetate  
Sec-Butyl formate
Sec-Butyl acetate  
Tert-Butyl formate  
Tert-Butyl acetate  
Butyl butyrate  

5 carbons edit

Name Structure
Amyl acetate  
Pentyl butyrate  
Pentyl propanoate
Pentyl hexanoate  
Sec-Amyl acetate  

7 carbons edit

Name Structure
Benzyl acetate  

8 carbons edit

Name Structure
Octyl acetate  

10 carbons edit

Name Structure
Geranyl acetate  
Bornyl acetate  
Linalyl acetate  

By number of R group carbons (R−C(=O)−O−R') edit

0 carbons edit

Name Structure
Methyl nitrate  

1 carbon edit

Name Structure
Methyl formate  
Ethyl formate  
Isobutyl formate  

2 carbons edit

Name Structure
Methyl acetate  
Ethyl acetate  
Propyl acetate  
Butyl acetate  
Amyl acetate  
Benzyl acetate  
Octyl acetate  
Geranyl acetate  
Bornyl acetate  
Linalyl acetate  

3 carbons edit

Name Structure
Methyl propionate  
Ethyl propionate  
Propyl propanoate  
Pentyl propanoate
Ethyl lactate  

4 carbons edit

Name Structure
Methyl butyrate  
Ethyl butyrate  
Butyl butyrate  
Pentyl butyrate  

5 carbons edit

Name Structure
Methyl pentanoate  
Ethyl pentanoate  
Pentyl pentanoate  
Ethyl isovalerate  

6 carbons edit

Name Structure
Ethyl hexanoate  
Propyl hexanoate  
Allyl hexanoate  
Pentyl hexanoate  

7 carbons edit

Name Structure
Ethyl heptanoate  
Methyl benzoate  
Ethyl benzoate  
Methyl anthranilate  
Methyl salicylate  
Ethyl salicylate  
Isopropyl salicylate  

8 carbons edit

Name Structure
Ethyl octanoate  
Methyl phenylacetate  

9 carbons edit

Name Structure
Methyl cinnamate  
Ethyl cinnamate  

10 carbons edit

Name Structure
Ethyl decanoate  

16 carbons edit

Name Structure
Isopropyl palmitate  

List of ester odorants edit

Many esters of carboxylic acid have distinctive fruit-like odors, and many occur naturally in fruits and the essential oils of plants. This has also led to their common use in artificial flavorings and fragrances which aim to mimic those odors.

Ester name Structure Odor or occurrence
Allyl hexanoate   pineapple
Benzyl acetate   pear, strawberry, jasmine
Bornyl acetate   pine
Butyl acetate   apple, honey
Butyl butyrate   pineapple
Butyl propanoate   pear drops
Ethyl acetate   nail polish remover, model paint, model airplane glue
Ethyl benzoate   sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate   banana, pineapple, strawberry
Ethyl hexanoate   pineapple, waxy-green banana
Ethyl cinnamate   cinnamon
Ethyl formate   lemon, rum, strawberry
Ethyl heptanoate   apricot, cherry, grape, raspberry
Ethyl isovalerate   apple
Ethyl lactate   butter, cream
Ethyl nonanoate   grape
Ethyl pentanoate   apple
Geranyl acetate   geranium
Geranyl butyrate   cherry
Geranyl pentanoate   apple
Isobutyl acetate   cherry, raspberry, strawberry
Isobutyl formate   raspberry
Isoamyl acetate   pear, banana (flavoring in Pear drops)
Isopropyl acetate   fruity
Linalyl acetate   lavender, sage
Linalyl butyrate   peach
Linalyl formate   apple, peach
Methyl acetate   glue
Methyl anthranilate   grape, jasmine
Methyl benzoate   fruity, ylang ylang, feijoa
Methyl butyrate (methyl butanoate)   pineapple, apple, strawberry
Methyl cinnamate   strawberry
Methyl pentanoate (methyl valerate)   flowery
Methyl phenylacetate   honey
Methyl salicylate (oil of wintergreen)   Modern root beer, wintergreen, Germolene and Ralgex ointments (UK)
Nonyl caprylate   orange
Octyl acetate   fruity-orange
Octyl butyrate   parsnip
Amyl acetate (pentyl acetate)   apple, banana
Pentyl butyrate (amyl butyrate)   apricot, pear, pineapple
Pentyl hexanoate (amyl caproate)   apple, pineapple
Pentyl pentanoate (amyl valerate)   apple
Propyl acetate   pear
Propyl hexanoate   blackberry, pineapple, cheese, wine
Propyl isobutyrate   rum
Terpenyl butyrate   cherry

Lactones edit

Lactones are a specific class cyclic carboxylic esters that are formed through intramolecular esterification.

Lactone name Structure
β-propiolactone  
γ-butyrolactone (GBL)
 
D-glucono-δ-lactone (E575)
 
ε-caprolactone
 

References edit

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "esters". doi:10.1351/goldbook.E02219
  2. ^ Cameron Wright (1986). A worker's guide to solvent hazards. The Group. p. 48. ISBN 9780969054542.
  3. ^ E. Richard Booser (21 December 1993). CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications. CRC. p. 237. ISBN 978-1-4200-5045-5.
  4. ^ Reichel, Marco; Krumm, Burkhard; Vishnevskiy, Yury V.; Blomeyer, Sebastian; Schwabedissen, Jan; Stammler, Hans‐Georg; Karaghiosoff, Konstantin; Mitzel, Norbert W. (2019-12-16). "Solid‐State and Gas‐Phase Structures and Energetic Properties of the Dangerous Methyl and Fluoromethyl Nitrates". Angewandte Chemie International Edition. 58 (51): 18557–18561. doi:10.1002/anie.201911300. ISSN 1433-7851. PMC 6916544. PMID 31573130.
  5. ^ Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_013
  6. ^ Merck Index, 12th Edition, 6089.
  7. ^ "Methyl Propionate Hazardous Substance Fact Sheet" (PDF). New Jersey Department of Health and Senior Services.
  8. ^ Methyl butyrate, thegoodscentscompany.com
  9. ^ Methyl pentanoate, thegoodscentscompany.com
  10. ^ Methyl benzoate, thegoodscentscompany.com
  11. ^ Methyl anthranilate, thegoodscentscompany.com
  12. ^ Methyl salicylate, thegoodscentscompany.com
  13. ^ Methyl phenylacetate, thegoodscentscompany.com
  14. ^ Methyl cinnamate, thegoodscentscompany.com
  15. ^ Ethyl formate, thegoodscentscompany.com
  16. ^ Ethyl acetate, thegoodscentscompany.com
  17. ^ Ethyl propionate, thegoodscentscompany.com
  18. ^ Ethyl lactate, thegoodscentscompany.com
  19. ^ Ethyl butyrate, thegoodscentscompany.com
  20. ^ Ethyl pentanoate, thegoodscentscompany.com
  21. ^ Ethyl isovalerate, thegoodscentscompany.com
  22. ^ Ethyl hexanoate, thegoodscentscompany.com
  23. ^ Ethyl heptanoate, thegoodscentscompany.com
  24. ^ Ethyl benzoate, thegoodscentscompany.com
  25. ^ Ethyl salicylate, thegoodscentscompany.com
  26. ^ Ethyl octanoate, thegoodscentscompany.com
  27. ^ Ethyl cinnamate, thegoodscentscompany.com
  28. ^ Ethyl decanoate, thegoodscentscompany.com